4,4-diphenyl-2-p-tolyl-3,1-benzoxazine | 59134-68-8

• 分子结构分类: 有机化合物 - 有机杂环化合物
• 英文名称: 4,4-diphenyl-2-p-tolyl-3,1-benzoxazine
• 英文别名: 4,4-diphenyl-2-p-tolyl-4H-3,1-benzoxazine；4,4-diphenyl-2-p-tolyl-4H-benzo[d][1,3]oxazine；2-(4-Methylphenyl)-4,4-diphenyl-3,1-benzoxazine
• CAS: 59134-68-8
• 化学式: C₂₇H₂₁NO
• 分子量: 375.47
• InChiKey: BTTJIUCKHOXYIZ-UHFFFAOYSA-N

物化性质

• 熔点：
  208 °C
• 沸点：
  512.9±60.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.5
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  21.6
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-[2-(Hydroxy-diphenyl-methyl)-phenyl]-4-methyl-benzamide 在 4,4'-二氨基二苯乙烯-2,2'-二磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以90%的产率得到4,4-diphenyl-2-p-tolyl-3,1-benzoxazine
  参考文献：
  名称：

  Synthesis of 4H-3,1-Benzoxazines by the Reaction of o-(N-Acylamino)benzyl Alcohols with DAST

  摘要：

  The treatment of o-(N-acylamino)benzyl alcohols (1) with DAST afforded the dehydrative cyclization product, 4H-3,1-benzoxazines (4) and the hydroxy replacement product, o-(N-acylamino)benzyl fluorides (5). The yields of benzoxazines (4) and fluorides (5) depend on the substituents at alpha-position and acyl groups. The treatment of alpha,alpha-diaryl-o-(N-acylamino)benzyl alcohols (1a-c) with DAST yielded benzoxazines (4a-c) exclusively, while that of alpha-monosubstituted o-(N-acylamino)benzyl alcohols (Id-k) with DAST yielded benzoxazines (4d-k) and fluorides (5d-k). In the reaction of o-(N-acylamino)benzyl alcohol (11) with DAST, the formation of fluoride (51) became predominant and that of benzoxazine (41) was suppressed almost completely.

  DOI：

  10.3987/com-05-s(t)22

文献信息

• Reaction of (1,ω)-<i>N</i>-Acylamino Alcohols with Lawesson's Reagent:  Synthesis of Sulfur-Containing Heterocycles
  作者：Takehiko Nishio

  DOI：10.1021/jo961704n

  日期：1997.2.1

  Lawesson's reagent [LR: 2,4-bis(p-methoxyphenyl)-1,3,2,4-dithiaphosphetane 2,4-disulfide] is shown to be a valuable reagent for the ready access of sulfur-containing heterocycles: thiazolines 2 starting from the (1,2)-N-acylamino alcohols 1 and benzothiazines 14 from [2-(N-acylamino)phenyl]alkanols 12. Treatment of (1,2)-N-acylamino secondary alcohols 1a-p with LR gave the thiazolines 1a-p via direct conversion of the alcohols to the respective thiols, and the subsequent thionation of the amide carbonyl, followed by cyclization with the elimination of hydrogen sulfide. However, reaction of (1,2)-N-acylamino tertiary alcohols 1q-u with LR yielded the dehydration products 5-7 and 9. Treatment of [2-(N-acylamino)phenyl]alkanols 12a-f with a molar equivalent of LR yielded the 3,1-benzothiazines 14a-f. In this reaction, the [2-(N-acylamino)phenyl]alkanethiols 13a-e were isolated when the corresponding alcohols 12a-e were treated with 0.5 equiv of LR. Further thionation of 13c with LR also gave 3,1-benzothiazine 14c.
• ALY, N. F.;FOULI, F. A.;ESSAWY, S. A.;ORABI, M. O., EGYPT. J. CHEM., 30,(1987) N, C. 435-440
  作者：ALY, N. F.、FOULI, F. A.、ESSAWY, S. A.、ORABI, M. O.

  DOI：——

  日期：——
• ZIMAITY T.; ANWAR M.; ABDEL-HAY F. I.; ABDEL-MEGEED M. F., ACTA CHIM. ACAD. SCI. HUNG. <ACAS-A2>, 1975, 87, NO 3, 251-255
  作者：ZIMAITY T.、 ANWAR M.、 ABDEL-HAY F. I.、 ABDEL-MEGEED M. F.

  DOI：——

  日期：——